AI Article Synopsis
- Four cyclic octapeptides were developed to study how different arrangements of oxazoline (Oxz) and thiazole (Thz) rings influence the structure and cell-killing ability (cytotoxicity) of these peptides.
- Cyclo(-Ile-Thz-D-Val-Oxz-) (2) switched ring positions compared to the original ascidiacyclamide (ASC, 1) while others varied the number of Oxz and Thz rings, leading to differing cytotoxic properties.
- The findings indicated that while some structures showed no cytotoxicity, peptide 3 exhibited a significantly higher cytotoxicity than the original, suggesting that the arrangement and quantity of Oxz rings play a crucial role in determining the effectiveness of ASC
Article Abstract
Four cyclic octapeptides were designed from ascidiacyclamide [cyclo(-Ile-Oxz-D-Val- Thz-) ] (ASC, 1) to investigate the effects of oxazoline (Oxz) and thiazole (Thz) rings on the structures and cytotoxicities of the peptides. cyclo(-Ile-Thz-D-Val-Oxz-) (2) had the same number of Oxz and Thz rings as ASC, but the ring positions were switched. cyclo(-Ile-Oxz-D-Val-Thz-Ile-Thz-D-Val-Thz-) (3) and cyclo(-Ile-Thz-D-Val-Oxz-Ile-Thz-D-Val-Thz-) (4) contained one Oxz and three Thz rings within the molecule. All Oxz rings were substituted with Thz in cyclo(-Ile-Thz-D-Val-Thz-) (5). These analogues had new Oxz and Thz blocks forming the 24-membered ring. Based on CD spectra and X-ray diffraction analyses, the structures of all four analogues were classified as square ASC forms. But the structures of 2 and 5 differed from the original square form of 1, and they showed no cytotoxicity. The structure of 3 was very similar to that of 1, and 3 showed 10 times greater cytotoxicity than 1. Although no definite structure of 4 was obtained, it showed three times greater cytotoxicity than 1. It appears that the position and number of Oxz residues are essential determinants in the structure-cytotoxicity relationship of ASC analogues.
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